The present invention relates to novel uses in foodstuffs and in foodstuff flavors of 3-furyl alkyl sulfides.
Artificial flavoring agents for foodstuffs have received increasing attention in recent years. In many areas, such food flavoring agents are preferred over natural flavoring agents at least in part because of the uniform flavor that may be so obtained. For example, natural food flavoring agents such as extracts, essences, concentrates and the like are often subject to wide variation due to changes in the quality, type and treatment of the raw materials. Such variation can be reflected in the end product and results in unreliable flavor characteristics and uncertainty as to consumer acceptance and cost. Additionally, the presence of the natural product in the ultimate food may be undesirable because of increased tendency to spoil. This is particularly troublesome in convenience and snack food usage where such products as dips, soups, chips, prepared dinners, canned foods, sauces, gravies and the like are apt to be stored by the consumer for some time prior to use.
The fundamental problem in preparing artificial flavoring agents is that of achieving as nearly as possible a true flavor reproduction. This generally proves to be a difficult task since the mechanism for flavor development in many foods is not understood. This is notable in products having meaty and roasted flavor characteristics.
Reproduction of sweet, meaty nutty, cereal-like, baked bread, liver-like, hydrolyzed protein-like, hazelnut, and pecan-like flavors and aromas has been the subject of the long and continuing search by those engaged in the production of foodstuffs. The severe storage of foods, especially protein foods, in many parts of the world has given rise to the need for utilizing non-meat sources of proteins and making such proteins as palatable and as meat-like as possible. Hence, materials which will closely simulate or exactly reproduce the flavor and aroma of roasted meat products and liver products are required.
Moreover, there are a great many meat containing or meat based food presently distributed in a preserved form. Examples being condensed soups, dry-soup mixes, dry meat, freeze-dried or lyophilized meats, packaged gravies and the like. While these products contain mat or meat extracts, the fragrance, taste and other organoleptic factors are very often impaired by the processing operation and it is desirable to supplement or enhance the flavors of these preserved foods with versatile materials which have either sweet, meaty, nutty, cereal-like, baked bread, liver-like, hydrolyzed vegetable protein-like, hazelnut or pecan-like aroma and taste nuances.
U.S. Pat. No. 3,666,495 has to do with certain furan derivatives having desirable meat, roast meat and fragrance and flavor notes. Among the furan derivatives disclosed in said patent are methyl (2-methyl-3-furyl) trisulfide obtained by the reaction of 2-methyl-3-furan thiol with methyl disulfur chloride at a temperature of from -60.degree. C to 0.degree. C, and methyl (2-methyl-3-furyl) disulfide obtained by reacting 2-methyl-3-furan thiol with methane sulfenyl chloride.
The organoleptic properties of such 3-furyl alkyl disulfides are different in flavor character and intensity from the organoleptic properties of 3-furyl alkyl sulfides of our invention.
U.S. Pat. No. 3,836,563 issued on Sept. 17, 1974 broadly discloses 3-furyl alkyl sulfides having the structure: ##STR2## wherein R.sub.9 ' may be alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl, n-octyl and n-nonyl (See Col. 4, lines 10-18), and R.sub.7 ', R.sub.8 ' and R.sub.9 ' are either hydrogen or alkyl. However, U.S. Pat. No. 3,836,563 does not contain claims drawn to such compounds or uses thereof and the subject matter claimed herein was invented by us prior to Aug. 7, 1973, the filing data of U.S. Pat. No. 3,836,563.
Danyushevskii, et al. J. Org. Chem. U.S.S.R., 6, 866-870 (1970) (Abstracted in Chem. Abstracts 70, 68020 (1969)) discloses compounds having the structure: ##STR3## (wherein R.sub.10 and R.sub.11 are lower alkyl) without describing any organoleptic properties thereof.